6116-76-3

Basic information

• Product Name: 3-ethyl-2-methyl-4,5,6,7-tetrahydroindol-4-one
• Synonyms: 3-ethyl-2-methyl-4,5,6,7-tetrahydroindol-4-one;3-ETHYL-2-METHYL-1,5,6,7-TETRAHYDRO INDOLE-4-ONE;3-ETHYL-2-METHYL-1,5,6,7-TETRAHYDROINDOL-4-ONE;3-ethyl-2-methyl-1,5,6,7-tetrahydro-4H-indol-4-one;2-Methyl-3-ethyl-4,5,6,7-tetrahydro-1H-indole-4-one;3-Ethyl-1,5,6,7-tetrahydro-2-methyl-4H-indol-4-one;3-ethyl-2-Methyl-6,7-dihydro-1H-indol-4(5H)-one;2-Methyl-3-ethyl-4-oxo-4,5,6,7-tetrahydroindole
• CAS NO: 6116-76-3
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.2429
• EINECS: 228-084-6
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 6116-76-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 183℃
• Boiling Point: 353.8°Cat760mmHg
• Flash Point: 175.6°C
• Appearance: /
• Density: 1.106
• Vapor Pressure: 3.49E-05mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 16.94±0.20(Predicted)
• CAS DataBase Reference: 3-ethyl-2-methyl-4,5,6,7-tetrahydroindol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ethyl-2-methyl-4,5,6,7-tetrahydroindol-4-one(6116-76-3)
• EPA Substance Registry System: 3-ethyl-2-methyl-4,5,6,7-tetrahydroindol-4-one(6116-76-3)

Safety Data

• Hazardous Substances Data: 6116-76-3(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Molindone intermediate.

InChI:InChI=1/C11H15NO/c1-3-8-7(2)12-9-5-4-6-10(13)11(8)9/h12H,3-6H2,1-2H3

Upstream product

• 98263-35-5 bis<3-ethyl-2-methyl-4,5,6,7-tetrahydroindol-4-ylidene>hydrazine 
• 35308-68-0 1,5,6,7-tetrahydro-2-methyl-4H-indol-4-one 
• 64-17-5 ethanol 
• 107-87-9 2-Pentanone 
• 815-48-5 3-bromopentan-2-one 
• 504-02-9 1,3-cylohexanedione 
• 13280-00-7 3-chloropentan-2-one 
• 130000-33-8 methyl 2-chloro-2-ethyl-3-oxobutanoate 
• 600-14-6 2,3-Pentanedione 
• 32818-79-4 2-(hydroxyimino)pentan-3-one 

Downstream Products

• 15622-65-8 molindone hydrochloride 
• 235426-07-0 N-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-4-(p-fluorobenzoyl)piperidine, bis ethylene ketal 
• 235426-02-5 N-(1-benzenesulfonyl-3-ethyl-2-methyl-4,5,6,7-tetrahydro-5-indolylethyl)-4-(p-fluorobenzoyl)piperidine, ethylene ketal 
• 165963-42-8 N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N⁴-(o-methoxyphenyl)piperazine 
• 165963-43-9 N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N⁴-(o-methoxyphenyl)piperazine 
• 235425-82-8 N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N⁴-(tert-butoxycarbonyl)piperazine 
• 165963-44-0 N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N⁴-(o-methoxyphenyl)piperazine 
• 235425-83-9 N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N⁴-phenylpiperazine 
• 235425-94-2 N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N⁴-phenylpiperazine 
• 235425-88-4 N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N⁴-phenylpiperazine 
• 235425-84-0 N-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)piperazine 
• 235425-92-0 N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolyl)ethyl>piperazine 
• 235425-86-2 N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>piperazine 
• 235425-98-6 N-(2-methyl-3-ethyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-4-(p-fluorobenzoyl)piperidine 

Relevant articles and documents

Catalytic Acceptorless Dehydrogenation of Amino Alcohols and 2-Hydroxybenzyl Alcohols for Annulation Reaction under Neutral Conditions

A base-free and acceptorless Ru-catalyzed dehydrogenative approach has been developed for the synthesis ofN-heterocycles by using 1,3-dicarbonyls and amino alcohols through a domino sequential enamine formation and intramolecular oxidative cyclization strategy. This unified approach is also applicable for the synthesis of O-heterocycles involving 2-hydroxybenzyl alcohol as a coupling reactant via consecutive C-alkylation and intramolecular cyclization steps. The present protocol is general for the synthesis of varieties of biologically important scaffolds, such as tetrahydro-4H-indol-4-one, 3,4-dihydroacridin-1(2H)-one, and tetrahydro-1H-xanthen-1-ones derivatives using a single catalytic system, viz. RuH2CO(PPh3)3. Environmentally benign H2O and H2are the only byproducts in this domino process. Moreover, RuH2CO(PPh3)3-catalyzed C3-alkylation of tetrahydro-4H-indol-4-one using alcohol as a alkylating partner is also described in this report. For the first time, a solvent-free gram-scale reaction for the acceptorless dehydrogenative annulation has been demonstrated. A plausible mechanism for the Ru-catalyzed base-free and acceptorless dehydrogenative annulation of amino alcohols or 2-hydroxybenzyl alcohols has been provided with several experimental investigations and spectroscopic evidence.

METHODS OF PRODUCING MOLINDONE AND ITS SALTS

The present invention is directed towards novel methods of synthesis of molindone, synthesis of the intermediates of molindone, and high-purity compositions of molindone. In particular, the invention relates to the methods of synthesis of molindone through the Mannich reaction.

Conformationally restricted butyrophenones with mixed dopaminergic (D2) and serotoninergic (5-HT(2A)) affinities. Synthesis of 5-aminoethyl-and 6- aminomethyl-4-oxotetrahydroindoles as potential atypical antipsychotics

We describe the synthesis of 5-aminoethyl- and 6-aminomethyl-4- oxotetrahydroindoles as butyrophenone derivatives in the indole series, as potential atypical antipsychotics. The affinities of these compounds for serotonin (5-HT(2A)) and dopamine (D2) receptors were evaluated in vitro. The ratios of pK(i)'s for 5-HT(2A)/D2 receptors may be useful for rapid screening of new compounds and assessing potential induction of extrapyramidal symptoms; ratio values ≥1.12 (Meltzer's ratio) are predictive of an atypical antipsychotic profile. Compounds 26e (QF 0408B) and 26f (QF 0409B) showed high affinity for both D2 and 5-HT(2A) receptors, and their Meltzer's ratios were 1.32 and 1.17 respectively, while haloperidol showed a ratio of 0.93.